Countryside Holidays from AU$1,788

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Your Countryside Holiday

From its rural countryside to its spectacular views and beyond, there's a lot to love about Countryside. Discover the wonders of this awesome city with a Countryside holiday package that's tailor-made for you. Fill your days with visits to Brookfield Zoo, SeatGeek Stadium and Chicago Ridge Shopping Mall, some of the attractions you shouldn't miss during your trip to Countryside. Check out Expedia's wide range of travel options and start planning your perfect holiday to Countryside today.

The Latest Countryside Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago

Grand Royal Hotel O'Hare - Chicago

3.5 out of 5
Price was AU$2,701, price is now AU$1,788 per person
AU$1,788
per person
19 Feb - 22 Feb
found 23 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
5.8/10 (215 reviews)
Friendly front desk, easy and convenient for my overnight layover in Chicago

Reviewed on 7 Nov 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was AU$3,209, price is now AU$2,099 per person
AU$2,099
per person
19 Feb - 22 Feb
found 23 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Stayed prior to flight, clean, quiet room!

Reviewed on 13 Jan 2026

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Price was AU$2,982, price is now AU$1,966 per person
AU$1,966
per person
19 Feb - 22 Feb
found 23 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
The sweetest staff ever! Very welcoming. Had a great stay!

Reviewed on 9 Jan 2026

Comfort Inn & Suites Arlington Heights - Schaumburg

Comfort Inn & Suites Arlington Heights - Schaumburg

3 out of 5
Price was AU$2,771, price is now AU$1,831 per person
AU$1,831
per person
19 Feb - 22 Feb
found 23 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (782 reviews)
Everything was excellent but they need to fix the Elevator the last time l was there in October its broken

Reviewed on 6 Jan 2026

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was AU$2,807, price is now AU$1,861 per person
AU$1,861
per person
19 Feb - 22 Feb
found 23 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
Hot water issue. Goy only Luke warm

Reviewed on 10 Jan 2026

Countryside Holiday

Countryside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
6,000
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Brookfield Zoo, Galloping Ghost and Madison Street Theatre

Our pick of the best Countryside Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 19 Jan to 20 Jan
AU$159
19 Jan - 20 Jan
includes taxes & fees
8/10 Very Good! (9,766 reviews)
Nice rooms. Everything is close by. Friendly and helpful staff

Reviewed on 12 Jan 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$272 per night from 2 Feb to 3 Feb
AU$272
2 Feb - 3 Feb
includes taxes & fees
8.4/10 Very Good! (2,523 reviews)
Yes great Hotel everything was perfect

Reviewed on 12 Jan 2026

Hilton Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 1 Feb to 2 Feb
AU$141
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (3,691 reviews)
Yes

Reviewed on 11 Jan 2026

Hilton Chicago/Magnificent Mile Suites
See all 5,121 properties in Countryside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Countryside

Navy Pier

Navy Pier

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Chicago Riverwalk featuring a bay or harbour, a city and a river or creek

Chicago Riverwalk

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk

What to do in Countryside

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$73
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
See all activities in Countryside

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.